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Synthetic studies toward (+)-CJ-12,950 for the stereochemical elucidation and structure activity relationship studies

Research Project

Project/Area Number 26460003
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Toyama

Principal Investigator

Sugimoto Kenji  富山大学, 大学院医学薬学研究部(薬学), 准教授 (60400264)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
KeywordsCJ-12,950 / 不斉全合成 / 閉環メタセシス / 大環状ラクトン / 構造決定 / 不斉合成 / マクロラクトン / 構造解明
Outline of Final Research Achievements

Based on the convergent synthetic strategy for CJ-12,950, we realized the total synthesis of a possible diastereomer of CJ-12,950. Sharpless asymmetric epoxidation and Keck asymmetric allylation were utilized for the construction of the key chiral centers on the macrolactone. Furthermore, we found that the Zhan-1b catalyst works much better than the Grubbs or Hoveyda-Grubbs catalyst for the ring closing metathesis and [Cp*RhCl2]2-mediated coupling reaction of O-pivaloyl hydroxamic acid with pinacol vinylboronate was critical for the pendant amide formation.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (12 results)

All 2016 2015 2014 Other

All Presentation (10 results) (of which Int'l Joint Research: 3 results) Remarks (2 results)

  • [Presentation] 構造活性相関研究を指向したCJ-12,950の不斉全合成研究2016

    • Author(s)
      小熊義史、山岸匠、山本のぞみ、篠田翔、杉本健士、高山亜紀、松谷裕二
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県金沢市
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of natural macrolide CJ-12,950 aiming at SAR studies for life-relating disease treatment2016

    • Author(s)
      小熊義史、山岸匠、山本のぞみ、篠田翔、杉本健士、松谷裕二
    • Organizer
      17th Tetrahedron Symposium
    • Place of Presentation
      スペイン/バルセロナ
    • Year and Date
      2016-06-28
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 立体化学の解明を目指した(+)-CJ-12,950の不斉全合成研究2016

    • Author(s)
      小熊義史、山岸匠、山本のぞみ、篠田翔、杉本健士、湊大志郎、松谷裕二
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic studies toward (+)-CJ-12,950 for the stereochemical assignment and structure activity relationship studies2015

    • Author(s)
      Oguma, Y.; Yamagishi, T.; Yamamoto, N.; Shinoda, S.; Sugimoto, K.; Toyooka, N.; Minato, D.; Matsuya, Y.
    • Organizer
      2015 International Congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii Convention Center他 (Hawaii, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 構造解明を目指したCJ-12,950の収束的合成経路の開拓2015

    • Author(s)
      小熊義史、山岸匠、山本のぞみ、杉本健士、湊大志郎、松谷裕二
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山)
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic Studies toward (+)-CJ-12,950 for the Stereochemical Assignment2015

    • Author(s)
      Oguma, Y.; Yamagishi, T.; Yamamoto, N.; Shinoda, S.; Sugimoto, K.; Minato, D.; Matsuya, Y.
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会議場(京都府京都市)
    • Year and Date
      2015-06-13
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 立体構造解明を目指したCJ-12,950の不斉全合成研究2015

    • Author(s)
      小熊義史,山岸匠,篠田 翔,山本のぞみ,豊岡尚樹,杉本健士,湊大志郎,松谷裕二
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学他(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 立体構造の解明及び構造活性相関研究を目指したCJ-12,950の収束的合成法の開発2014

    • Author(s)
      小熊義史,山岸匠,山本のぞみ,篠田 翔,豊岡尚樹,杉本健士,湊大志郎,松谷裕二
    • Organizer
      日本薬学会北陸支部第126回例会
    • Place of Presentation
      金沢大学(石川県金沢市)
    • Year and Date
      2014-11-16
    • Related Report
      2014 Research-status Report
  • [Presentation] 構造解明を目指したCJ-12,950 の収束的合成経路の開拓2014

    • Author(s)
      山岸匠,小熊義史,山本のぞみ,篠田翔,豊岡尚樹,杉本健士,湊大志郎,松谷裕二
    • Organizer
      平成26年度有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県坂井市)
    • Year and Date
      2014-10-03 – 2014-10-04
    • Related Report
      2014 Research-status Report
  • [Presentation] 三次元構造の解明を目指したCJ-12,950の不斉全合成研究2014

    • Author(s)
      小熊義史,山岸匠,山本のぞみ,篠田 翔,大木貴博,杉本健士,豊岡尚樹,湊大志郎,松谷裕二
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール(北海道札幌市)
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Research-status Report
  • [Remarks] 所属研究室ホームページ

    • URL

      http://www.pha.u-toyama.ac.jp/mediche2/seizou_jp/Home.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 富山大学薬学部/大学院医学薬学研究部 薬品製造学研究室

    • URL

      http://www.pha.u-toyama.ac.jp/mediche2/seizou_jp/Home.html

    • Related Report
      2015 Research-status Report 2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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